Acetic Acid → HCID 86737173, compound

HRID 1856580Notes

Reaction equation

HRID 1856580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][S:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.OO.[OH-:39].[Na+].[C:41]([OH:44])(=[O:43])[CH3:42]>>[C:41]([OH:44])(=[O:43])[C:42]([OH:35])=[O:39].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][S:28]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)(=[O:43])=[O:39])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12891577HCID 12891577, compound

Product 1

HCID 86737173HCID 86737173, compoundYield 16%

Procedure

A mixture of 3.7 parts of 1-(4-fluorophenylmethyl)-N-{1-[3-(4-methoxyphenylthio)propyl]-4-piperidinyl}-1H-benzimidazol-2-amine, 2.42 parts of hydrogen peroxide solution 30% and 20 parts of acetic acid is stirred and refluxed for 1 hour. The reaction mixture is cooled and poured onto ice-water. The whole is alkalized with sodium hydroxide solution 50% and the product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in methanol and 2-propanol. The salt is filtered off and dried, yielding 0.8 parts (16%) of 1-(4-fluorophenylmethyl)-N-{1-[3-(4-methoxyphenylsulfonyl)propyl]-4-piperidinyl}-1H-benzimidazol-2-amine ethanedioate (1:2); mp. 213.1° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto ice-water
  4. extractionthe product is extracted with trichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. filtrationThe salt is filtered off
  14. customdried

Sources & evidence

ORD record
ord-6c82d85dac7746578f227233fe662e64
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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